EP2073288A2 - Composition de couche d'isolation de porte en polymère organique et transistor de film mince organique l'utilisant - Google Patents

Composition de couche d'isolation de porte en polymère organique et transistor de film mince organique l'utilisant Download PDF

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Publication number
EP2073288A2
EP2073288A2 EP08162406A EP08162406A EP2073288A2 EP 2073288 A2 EP2073288 A2 EP 2073288A2 EP 08162406 A EP08162406 A EP 08162406A EP 08162406 A EP08162406 A EP 08162406A EP 2073288 A2 EP2073288 A2 EP 2073288A2
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EP
European Patent Office
Prior art keywords
insulating layer
composition
gate insulating
organic polymer
otft
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP08162406A
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German (de)
English (en)
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EP2073288A3 (fr
Inventor
Seong Hyun Kim
Sang Chul Lim
Gi Heon Kim
Ji Ho Youk
Tae Gon Kim
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Electronics and Telecommunications Research Institute ETRI
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Electronics and Telecommunications Research Institute ETRI
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Publication of EP2073288A2 publication Critical patent/EP2073288A2/fr
Publication of EP2073288A3 publication Critical patent/EP2073288A3/fr
Withdrawn legal-status Critical Current

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
    • H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate

Definitions

  • the present invention relates to a composition for an organic polymer gate insulating layer and an Organic Thin Film Transistor (OTFT) using the same, and more particularly, to a composition for a photoreactive organic polymer gate insulating layer that can be micropatterned and an OTFT using the composition.
  • OTFT Organic Thin Film Transistor
  • OTFTs are expected to be frequently used in actuation devices of plastic-based active Organic Light Emitting Devices (OLEDs), smartcards, and plastic chips for inventory tags, and thus are currently being researched in the foremost companies, research institutes, universities, and so on.
  • OTFT performance is evaluated in terms of field effect mobility, an on/off ratio, mobility, a subthreshold slope, and so on.
  • OTFT performance is influenced by the degree of crystallization of an organic active layer, an electric charge characteristic of an interface between an organic insulating layer and the organic active layer, a thin film characteristic of the organic insulating layer, a carrier injection capability of an interface between source and drain electrodes and the organic active layer, and so on. To improve these characteristics, various methods are being tried out.
  • a material having low electrical conductivity and a high breakdown field is required.
  • silicon oxide layers are used as gate insulating layers of OTFTs.
  • an inorganic insulating layer is applied to an OTFT, physical/chemical characteristics of a substrate (particularly, plastic substrates) and other layers, i.e., previously-processed layers formed on the substrate in previous processes, are affected by high temperature required to form the inorganic insulating layer, and characteristics of the OTFT may deteriorate. Therefore, research is underway into a new organic gate insulating layer that can be formed through a low-temperature process and thus minimize deterioration of previously-processed layers,
  • polyimide Korean Patent Publication No. 2003-0016981
  • polyvinylalcohol PVA
  • poly(vinyl phenol-maleimide) Korean Patent Publication No. 2004-0028010
  • photoacryl etc.
  • organic insulating layers but do not have as good device characteristics as an inorganic insulating layer. Therefore, in order to implement a highly efficient OTFT, an organic gate insulating layer which can be formed thin through a simplified process without affecting a substrate and previously-processed layers, as well as a material for an organic active layer, must be developed.
  • the present invention is directed to providing a composition for an organic polymer gate insulating layer which has photocrosslinking characteristics capable of micropatterning, and can improve electrical characteristics.
  • the present invention is also directed to providing an Organic Thin Film Transistor (OTFT) including the organic polymer gate insulating layer to improve device characteristics.
  • OTFT Organic Thin Film Transistor
  • composition for an organic polymer gate insulating layer including: an insulating organic polymer including at least one selected from the group consisting of polymethylmethacrylate (PMMA), polyvinylalcohol (PVA), polyvinylpyrrolidone (PVP), poly(vinyl phenol) (PVPh) and a copolymer thereof; a crosslinking monomer having two or more double bonds; and a photoinitiator.
  • PMMA polymethylmethacrylate
  • PVA polyvinylalcohol
  • PVP polyvinylpyrrolidone
  • PVh poly(vinyl phenol)
  • an OTFT including: an organic polymer gate insulating layer formed by dissolving a composition for an organic polymer gate insulating layer in a solvent.
  • the composition for an organic polymer gate insulating layer includes: an insulating organic polymer including at least one selected from the group consisting of PMMA, PVA, PVP, PVPh and a copolymer thereof; a crosslinking monomer having two or more double bonds; and a photoinitiator.
  • FIG. 1 shows an image of a Polymethylmethacrylate (PMMA)-based organic polymer gate insulating layer patterned by lithography according to an exemplary embodiment of the present invention
  • FIG. 2 shows current-voltage (I-V) curves illustrating field-effect mobility of an Organic Thin Film Transistor (OTFT) according to an exemplary embodiment of the present invention
  • FIG. 3 shows an image of a PMMA copolymer-based organic polymer gate insulating layer patterned by lithography according to another exemplary embodiment of the present invention.
  • a composition for a photoreactive polymer gate insulating layer including an insulating organic polymer, a crosslinking monomer having two or more double bonds, and a photoinitiator, is provided.
  • the insulating organic polymer may be one or more selected from polymethylmethacrylate (PMMA), polyvinylalcohol (PVA), polyvinylpyrrolidone (PVP), poly(vinyl phenol) (PVPh) shown in chemical formulae 1 to 4 below, and a copolymer thereof.
  • PMMA polymethylmethacrylate
  • PVA polyvinylalcohol
  • PVP polyvinylpyrrolidone
  • PVPh poly(vinyl phenol) shown in chemical formulae 1 to 4 below, and a copolymer thereof.
  • the degree of polymerization of the polymers may be determined according to their intended use.
  • the degree of polymerization of the polymers is at least 50 and may be 100 to 1000.
  • the copolymers include, but is not limited to, poly(methylmethacrylate-random-viny 1 alcohol), poly(methylmethacrylate-random-vinyl pyrrolidone), poly(methylmethacrylate-random-vinyl phenol), poly(vinyl alcohol-random-vinyl pyrrolidone), or poly(vinyl pirrolidone-random-vinyl phenol).
  • the copolymerization ratio of the copolymers can be 1/99 to 99/1.
  • the insulating organic polymer may be present in an amount of 1 or more weight %, and preferably from 5 to 50 weight %, based on the total composition weight.
  • the crosslinking monomer having two or more double bonds may be selected from those shown in chemical formulae 5 to 8 below. [Chemical Formula 5] R'-R-R'
  • R" is -H, -CH 3 , - CH 2 CH 3 , etc.
  • pentaerythritol tetraacrylate or dipentaerythritol hexaacrylate shown in chemical formulae 9 and 10 below may be better.
  • the crosslinking monomer may be present in an amount of 1 or more weight %, and preferably from 5 to 50 weight %, based on the total composition weight.
  • crosslinking monomer of 1 or more weight % based on the total composition weight is included, it is possible to form a gate insulating layer of a semi-interpenetrating polymer network that can be micropatterned and has excellent chemical resistance and thermal resistance.
  • the photoinitiator of 0.1 or more weight % based on the total composition weight must be added to cause a photoreaction, and the photoinitiator may be preferably added in range of 0.25 to 3.5 weight %.
  • the other material may be an insulating organic polymer.
  • thermoinitiator In the composition for a gate insulating layer, a thermoinitiator may be further included.
  • the thermoinitiator must be added in an amount of 0.1 or more weight parts based on 100 weight % of the composition weight, and the thermoinitiator may be added in range of 0.25 to 3.5 weight parts.
  • the insulating organic polymer, the crosslinking monomer, the photoinitiator and the thermoinitiator may be dissolved in a solvent, e.g., propylene glycol monomethyl ether acetate or ethyl-3-ethoxypropionate, at a concentration of 1 or more weight %, and used.
  • a solvent e.g., propylene glycol monomethyl ether acetate or ethyl-3-ethoxypropionate
  • concentration of the polymer must be 1 or more weight % to ensure a coating characteristic and the thickness of a thin film.
  • the insulating organic polymer may be used as a homopolymer in a gate insulating layer, or may be physically blended with another homopolymer having an excellent insulation characteristic and used in consideration of physical, chemical and electrical characteristics of an organic insulating layer.
  • composition for a photoreactive organic polymer gate insulating layer has a photochemical characteristic enabling micropatterning. And, using a thermoinitiator, additional crosslinks of double bonds remaining after patterning enable leakage current to be reduced and electrical characteristics to be improved.
  • the quantity of the photoinitiator and the thermoinitiator may be appropriately determined according to a purpose, a use, elements and a quantity of the composition.
  • the photoinitiator is activated by rays of visible wavelength, and may be selected from the following materials:
  • Irgacure 500 including 50 weight % of Irgacure 184C and 50 weight % of benzophenone;
  • Irgacure 1000 including 20 weight % of Irgacure 184C and 80 weight % of Darocur 1173;
  • Irgacure 1300 including 30 weight % of Irgacure 369 and 70 weight % of Irgacure 651;
  • Diphenyl (2,4,6-trimethylbenzoyl)-phosphine oxide (Darocur TPO);
  • Irgacure 2005 including 5 weight % of Irgacure 819 and 95 weight % of Darocur 1173;
  • Irgacure 2010 including 10 weight % of Irgacure 819 and 90 weight % of Darocur 1173;
  • Irgacure 2020 including 20 weight % of Irgacure 819 and 80 weight % of Darocur 1173.
  • thermoinitiator is activated by heat.
  • the thermoinitiator may be selected from the following materials and, in particular, may be a high-temperature radical initiator generating a radical in second baking:
  • BP Benzoyl peroxide
  • t-BTP Di-tert-butyl peroxide
  • An Organic Thin Film Transistor has a structure in which a substrate, a gate electrode, a gate insulating layer, an organic active layer and source and drain electrodes are stacked in sequence, or a substrate, a gate electrode, a gate insulating layer, source and drain electrodes and an organic active layer are stacked in sequence.
  • the structure is not limited to these, and the OTFT may have other structures also.
  • the substrate is one that is generally used in this field.
  • glass, silicon wafer, plastic, etc. may be used for the substrate, but the material of the substrate is not limited to these.
  • the gate electrode is formed on the substrate by a method generally used in this field, e.g., an e-beam technique, using a shadow mask.
  • a metal generally used in this field may be used.
  • the metal may include Au, Ah, Ni, Indium-Tin-Oxide (ITO), Al, Ti, TiN and Cr, but is not limited to these.
  • the gate insulating layer is formed through photocrosslinking and thermal crosslinking of a composition obtained by dissolving PMMA, PVA, PVP, PVPh or a copolymer thereof, a crosslinking monomer having two or more double bonds, a photoinitiator and a thermoinitiator in an appropriate solvent.
  • the photoreactive organic polymer gate insulating layer is formed on the gate electrode through a wet process.
  • the composition for a gate insulating layer is coated through spin coating, dipping or printing, baked to form the insulating layer.
  • the organic polymer gate insulating layer is patterned through a development process after forming a semi-interpenetrating polymer network by crosslinking. Images of crosslinking organic polymer gate insulating layers patterned by lithography are shown in FIGS. 1 and 3 .
  • the organic active layer may be formed of a general material, such as pentacene, dihexyl-hexythiophene (DH6T), regioregular poly(3-hexylthiophene) (P3HT), poly-9,9-dioctylfluorenc-co-bithiophene (F8T2), and dihexylanthra-dithiophene (DHADT), or a derivative thereof.
  • the material forming the organic active layer is not limited to these.
  • the organic active layer may be formed under conditions generally known in this field, by the same method as used to deposit the materials.
  • the source and drain electrodes may be formed of a general metal, such as Au, ITO, Al and Cr, but the material is not limited to these.
  • the source and drain electrodes are formed on the organic active layer by a method generally known in this field, which may be the e-beam technique using a shadow mask.
  • the substrate, the gate electrode, the gate insulating layer, the organic active layer and the source and drain electrodes may be formed to respective thicknesses generally used in this field.
  • composition for a photoreactive organic polymer gate insulating laver Preparation of composition for a photoreactive organic polymer gate insulating laver.
  • PMMA as a high-permittivity organic polymer
  • dipentaerythritol hexaacrylate as a crosslinking monomer
  • trimethylbenzen diphenyl phosphine oxide as a photoinitiator, corresponding to a weight ratio of 1.0/1.0/0.2, were dissolved in propylene glycol monomethyl ether acetate at a concentration of 25 weight % to prepare the composition for an organic polymer gate insulating layer.
  • a gate insulating layer formed by actual photocrosslinking comprises a semi-interpenetrating polymer network. The formed thin film was developed using ethyl acetate, and thereby a polymer gate insulating layer having a fine film was formed.
  • the polymer gate insulating layer was baked at 200 °C for 10 minutes.
  • the thickness of the final organic polymer gate insulating layer was 15500 ⁇ .
  • pentacene was deposited to a thickness of 800 ⁇ under conditions of high vacuum ( ⁇ 1.0 ⁇ 10 -6 torr), a substrate temperature of 70 °C, and a deposition rate of 1 ⁇ /sec, and thereby a pentacene active layer was formed.
  • Au was deposited to have a channel width of 2 mm, a channel length of 50 ⁇ m, and a thickness of 500 ⁇ as source and drain electrodes.
  • FIG. 1 shows an example of a fine pattern formed by photocrosslinking the composition for a photoreactive organic polymer gate insulating layer made in Exemplary embodiment 1.
  • FIG. 2 The characteristic graphs of FIG. 2 illustrate drain current-drain voltage (ID-VD) characteristics of a typical transistor.
  • IDS WCi / 2 ⁇ L ⁇ VGS - VT 2
  • W and L denote the width and length of source and drain electrodes
  • ⁇ , Ci and VT denote a degree of field-effect mobility, a capacitance of an insulator and a threshold voltage.
  • PMMA as a high-permittivity organic polymer
  • pentaerythritol tetraacrylate as a crosslinking monomer
  • trimethylbenzen diphenyl phosphine oxide as a photoinitiator
  • dicumyl peroxide as a thermoinitiator, corresponding to a weight ratio of 1.0/1.0/0.1/0.2, were dissolved in propylene glycol monomethyl ether acetate at a concentration of 25 weight % to prepare a composition for an organic polymer gate insulating layer.
  • An OTFT was fabricated in the same way as in Exemplary embodiment 1.
  • the thickness of the final organic polymer gate insulating layer was 4000 ⁇ .
  • the fabricated device had the ID-VD characteristics of a typical transistor, and the field-effect mobility of this exemplary embodiment was determined to be 0.28 cm 2 /Vs.
  • compositions for a photoreactive organic polymer gate electrode were formed using poly(methylmethacrylate-random-vinyl phenol) (50 moles/50 moles) or poly(methylmethacrylate-random-vinyl pyrrolidone) (50 moles/50 moles) instead of the PMMA of Exemplary embodiment 1 (see Table 1 below).
  • An OTFT was fabricated in the same way as in Exemplary embodiment 1.
  • the thickness of an organic polymer gate insulating layer is shown in Table 1.
  • the thickness of the final organic polymer gate insulating layer and a field-effect mobility determined in these exemplary embodiments are shown in Table 1.
  • Table 1 Gate Insulating Layer Organic Polymer Crosslinking Monomer Concentration of Composition (wt %) Thickness of Cate insulating Layer ( ⁇ ) Field-Effeet Mobility (cm 2 /Vs)
  • Exemplary Embodiment 3 Poly(methylmethacrytate-random-vinyl phenol) Pentaerythritol triacrylate 31 4800 0.23
  • Exemplary Embodiment 4 Poly(methylmethacrylate-random-vinyl phenol) Dipentaerythritol hexaacrylate 31 6000 0.35
  • Exemplary Embodiment 5 Poly(methylmethacrylate-random-vinyl pyrrolidone) Pentaerythritol triacrylate 25 8200 0.65
  • Exemplary Embodiment 6 Poly(methylmethacrylate-random-vinyl pyrrolidone)
  • composition for a photoreactive organic polymer gate insulating layer and the OTFT using the same have the following effects.
  • composition for a photoreactive organic polymer gate insulating layer constitutes a polymer layer that can be processed by photolithography.
  • composition for a photoreactive organic polymer gate insulating layer is micropatterned through a low-temperature photolithography process such that deterioration of a previously-processed layer is minimized.
  • the OTFT according to an exemplary embodiment of the present invention uses a variety of previously-processed layers due to a photoreactive organic polymer gate insulating layer, such that the structure of the OTFT can be diversified.
  • composition for a photoreactive organic polymer gate insulating layer according to an exemplary embodiment of the present invention is formed through a wet process, and thus it is preferable to fabricate OTFTs on a large substrate.
  • the composition includes an insulating organic polymer including at least one selected from the group consisting of polymethylmethacrylate (PMMA), polyvinylalcohol (PVA), polyvinylpyrrolidone (PVP), poly(vinyl phenol) (PVPh) and a copolymer thereof, a crosslinking monomer having two or more double bonds, and a photoinitiator.
  • PMMA polymethylmethacrylate
  • PVA polyvinylalcohol
  • PVP polyvinylpyrrolidone
  • PVPh poly(vinyl phenol)
  • the OTFT includes a gate insulating layer of a semi-interpenetrating polymer network formed of the composition.
  • composition for a photoreactive organic polymer gate insulating layer has a photochemical characteristic that enables micropatterning, and can be formed into a layer having excellent chemical resistance, thermal resistance, surface characteristics and electrical characteristics.

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  • Thin Film Transistor (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Formation Of Insulating Films (AREA)
EP08162406A 2007-12-17 2008-08-14 Composition de couche d'isolation de porte en polymère organique et transistor de film mince organique l'utilisant Withdrawn EP2073288A3 (fr)

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KR1020070132734A KR20090065254A (ko) 2007-12-17 2007-12-17 광반응성 유기고분자 게이트 절연막 조성물 및 이를 이용한유기 박막 트랜지스터

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SG11201405938VA (en) 2012-03-22 2014-11-27 3M Innovative Properties Co Polymethylmethacrylate based hardcoat composition and coated article
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WO2015188181A1 (fr) * 2014-06-06 2015-12-10 Polyera Corporation Transistors à oxyde métallique auto-alignés et leurs procédés de fabrication
WO2015191293A1 (fr) 2014-06-11 2015-12-17 Eastman Kodak Company Dispostifs dotés de couches diélectriques polymériques de thiosulfate
US11156622B2 (en) 2016-04-05 2021-10-26 The Trustees Of Dartmouth College Molecularly-imprinted-polymer coated conductive nanoparticles for cotinine detection, and associated devices and methods
JPWO2018131495A1 (ja) * 2017-01-10 2019-11-07 Ｊｓｒ株式会社 カバー膜形成方法、基材の処理方法及び組成物
CN113410384B (zh) * 2021-06-28 2023-04-07 西南大学 一种用于柔性场效应晶体管的聚合物介电层的制备方法

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JP5097644B2 (ja) 2012-12-12
KR20090065254A (ko) 2009-06-22
US20090152537A1 (en) 2009-06-18
JP2009147294A (ja) 2009-07-02
US7741635B2 (en) 2010-06-22
EP2073288A3 (fr) 2011-06-15

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